How Would Jack Kerouac Dress in This Decade?

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Imagine yourself hunched over a typewriter in your apartment, tapping away on a 10-foot-long scroll of paper, going through endless notes you've written in an attempt to finally get your damn thoughts out. As prolific as he was, that was Kerouac's way of working. And, although he was originally met with criticism and had trouble finding a publisher, he would eventually become the voice of a generation — the beat generation.

He published often, but On The Road still stands out. Sections on drug use, homosexuality, and various taboo subjects (at the time, at least) made it that much harder for Kerouac to get the work published once he finished it in 1951; it didn't help that the manuscript was one continuous paragraph on that very long sheet roll. But once it eventually hit shelves in 1957, the author became an instant celebrity — something he never wanted and, reportedly, didn't really enjoy. For one, people started paying a lot of his attention to his casually elegant style, a way of getting dressed that still feels modern today. And while On The Road inspired writers, artists, and musicians for many years to come, The Style Blog's still inspired by his wardrobe choices. Click below to see what I mean, with a slideshow of imagined outfits Kerouac might wear if he were still with us today...